تفاعل #524564

معادلة التفاعل

sodium iodide

γ-Chlorobutyrophenone

cis-2,6-dimethylpiperidine

→

cis-γ-(2,6-dimethylpiperidino)butyrophenone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of 619 g
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةat reflux for 48 hours
4. 4
   درجة الحرارةThe mixture is cooled
5. 5
   workup.ADDITIONdiluted with 1 l
6. 6
   ترشيحof anhydrous ether and filtered
7. 7
   أخرىto remove cis-2,6-dimethylpiperidine hydrochloride
8. 8
   غسيلThe filter cake is washed with 1 l
9. 9
   غسيلThe resulting ether solution is washed five times with 500 ml
10. 10
    استخلاصportions of water, then extracted with a solution of 300 ml
11. 11
    استخلاصThe acid extract
12. 12
    غسيلis washed with 500 ml
13. 13
    درجة الحرارةof ether, then heated to 70°-80°
14. 14
    أخرىthe organic layer is separated
15. 15
    استخلاصThe aqueous layer is extracted with 500 ml
16. 16
    استخلاصThe combined extract
17. 17
    غسيلis washed several times with water
18. 18
    أخرىdried
19. 19
    أخرىevaporated
20. 20
    workup.DISTILLATIONThe oily residue is distilled at reduced pressure

الإجراء التجريبي

A mixture of 619 g. of γ-Chlorobutyrophenone, ethylene ketal, 700 g. of cis-2,6-dimethylpiperidine and 16 g. of sodium iodide is stirred and heated at reflux for 48 hours. The mixture is cooled, diluted with 1 l. of anhydrous ether and filtered to remove cis-2,6-dimethylpiperidine hydrochloride. The filter cake is washed with 1 l. of ether and the filtrate and washings combined. The resulting ether solution is washed five times with 500 ml. portions of water, then extracted with a solution of 300 ml. of concentrated hydrochloric acid in 3 l. of water. The acid extract is washed with 500 ml. of ether, then heated to 70°-80° and allowed to cool to room temperature over a period of 16 hours. The resulting solution is basified with 50% aqueous sodium hydroxide and the organic layer is separated. The aqueous layer is extracted with 500 ml. of ether and the extract is combined with the organic layer. The combined extract is washed several times with water, dried and evaporated. The oily residue is distilled at reduced pressure to give cis-γ-(2,6-dimethylpiperidino)butyrophenone; b.p. 138°-141° C./0.1 mm.

المصدر